Oakland Hills Homes with Sidewalk Exterior Features

Welcome to Oakland Hills, a picturesque subdivision nestled in the heart of Winter Garden, Florida, within the vibrant Orange County. This charming community perfectly blends suburban tranquility with urban convenience, making it an ideal place for families, professionals, and retirees alike.

Oakland Hills boasts beautifully designed homes that feature inviting sidewalks, encouraging a sense of community and promoting an active lifestyle. Picture yourself taking leisurely strolls along tree-lined streets, where neighbors greet one another and children play freely. The sidewalks not only enhance the neighborhood’s aesthetic appeal but also provide safe pathways for walking, jogging, or biking, making it easy to enjoy the outdoors.

The homes in Oakland Hills are a testament to modern living, offering a variety of floor plans that cater to diverse tastes and lifestyles. With spacious layouts, contemporary finishes, and well-manicured lawns, these residences are designed for comfort and functionality. Many homes come equipped with energy-efficient appliances and smart home technologies, ensuring that your living experience is both enjoyable and sustainable.

Located just minutes from the vibrant downtown Winter Garden, residents of Oakland Hills have easy access to an array of shopping, dining, and entertainment options. The nearby West Orange Trail offers endless opportunities for outdoor adventures, while the community itself hosts various events that foster a strong neighborhood spirit.

If you’re looking for a welcoming community with beautiful homes and a friendly atmosphere, Oakland Hills in Winter Garden is the perfect place to call home. Come explore the charm and convenience of this delightful subdivision today!

Newest Oakland Hills Homes with Sidewalk Exterior Features

$2,325,000

4 Beds ⋅ 5 Baths ⋅ Oakland Hills SubDv. ⋅ 34787 Zip Code

Perfectly positioned on a quiet cul-de-sac in the sought-after Oakland Hills community near historic downtown Winter Garden. This FULLY FURNISHED and thoughtfully designed custom home on a single level, combines timeless modern farmhouse architecture with today's finest technology and craftsmanship. Curb appeal abounds with a classic mix of Hardie board siding and brick, anchored by a large, shaded front porch glowing with authentic gas lanterns from New Orleans — a true farmhouse welcome. When evening arrives, intentional landscape lighting accentuates the lush grounds and craftsmanship evident in every corner. Inside, the statement grand great room makes an unforgettable first impression with soaring 22+ foot ceilings, exposed beams, and dormer windows that fill the room with natural sunlight from morning to evening. Throughout the home, ten-foot ceilings, custom moldings and baseboards, LBU lighting with LED bulbs, and natural hardwood floors (in all but the media room) keep the ambiance light and welcoming. The heart of this custom residence is a true chef's kitchen: Monogram appliances, two oversized islands, a 36" gas range, paired with Moen and Kohler fixtures, all wrapped in custom Wellborn cabinetry with soft-close doors and drawers. A back second kitchen — the ultimate working pantry — adds double ovens, a microwave, a commercial Keurig, and abundant storage for effortless entertaining. Just off the main living space, a warm and welcoming library/office with custom-built bookcases and Zoom room offers a quiet retreat. The generous primary suite is a luxurious escape, complete with a spa-inspired bathroom centered around an oversized Kohler clawfoot tub. Two additional guest suites offer king beds and ensuite baths with double vanities, while a thoughfully designed bunk room with its own private bath means every guest feels right at home. Movie nights reach a new level in the dedicated media room with a 4K projector and Atmos surround sound. Outdoor living takes center stage on the expansive covered lanai, where a fully equipped summer kitchen with 36" Coyote natural gas grill, exhaust vent, steel doors, and retractable screen — makes alfresco entertaining effortless. Beyond, a private backyard with a heated pool and natural gas fire pit invites year-round gatherings that won't be forgotten. Enjoy smart home living at it's best with a Crestron home automation system, WattBox® UPS battery, Uniview Turret security cameras monitored by Future Home Integration, plus whole-home Wi-Fi with service options from Spectrum or Quantum. Custom closets, two laundry rooms, and an oversized three-car garage with an incredible amount of extra storage. Oakland Hills is an exclusive enclave of just 17 custom homes, minutes from the West Orange Trail, downtown Winter Garden, and Winter Garden Village. Perfectly positioned with easy access to the Turnpike, SR 429, and SR 408, it makes commuting, theme park visits, and airport runs a breeze. Schedule your private tour today and experience everything this meticulous one-of-a-kind home has to offer!

15217 Farm Stand Court, Winter Garden

$400,000

3 Beds ⋅ 2 Baths ⋅ Oakland Hills SubDv. ⋅ 33619 Zip Code

Experience modern luxury and coastal elegance in this brand-new, steel-frame construction masterpiece. This stunning three-bedroom, two-bathroom home combines structural integrity with high-end designer finishes, offering a low-maintenance lifestyle perfectly situated for a quick commute to MacDill AFB and Downtown Tampa. The interior is defined by a wide-open floor plan with soaring vaulted ceilings accented by a rustic wood beam, creating an airy and sophisticated atmosphere. Durable flooring flows seamlessly throughout the entire home with absolutely no carpet to be found. The kitchen serves as a gourmet centerpiece, featuring a spacious layout with all-new cabinetry, sleek quartz countertops, and a full suite of new stainless steel appliances. While the living area is impressive, the bathrooms are the undisputed star of the show, both featuring exquisite floor-to-ceiling porcelain tile and designer gold-tone fixtures plus back lit, fog-less mirrors. The primary suite is a true retreat, boasting a large walk-in closet and an ensuite bathroom with a massive walk-in shower equipped with a luxury rain shower head. The guest bathroom is equally impressive, featuring a deep-soaking freestanding tub with shower wand, that adds a spa-like feel for family or visitors. Practicality meets comfort with the inclusion of an energy-efficient tankless water heater and a brand-new septic system. The exterior living spaces are just as inviting, highlighted by a large covered front porch and a fully fenced-in backyard. This home is a rare blend of modern industrial strength and sophisticated interior design, offering a turnkey opportunity in a prime location.

6510 E 23rd Avenue, Tampa

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